It was only 10 days ago, on a Friday evening after work, when I learned my internet friend Dumpster Doggy was going to be in New York City for a week, visiting her friend from college this week. It made me think “I’ve never flown across the country to visit a friend before” and “I should totally do that sometime!” In that instant, I remembered that my new job affords me the benefit of a paid holiday for Veteran’s Day, which was coming up the following weekend, and observed on the Monday (today) that I write this. A three-day weekend – I should totally take advantage of that extra day and travel somewhere!

Being somewhat unimaginative myself, I borrowed Dumpster Doggy’s idea – I would travel to NYC! As you are probably aware by now, I have tons of points and miles from various hotel and airline programs, plus the beneficial “transferable points” from a couple different bank/credit card programs. So, I set out searching for routes and times for flights that would work, and award availability at hotels in the City that would make for spectacular redemptions.

As a cardholder of the Chase IHG credit card, I receive a certificate good for a free night at any hotel in their portfolio around the world. They have recently changed the terms to make it work for hotels with a maximum of 40,000 IHG points per night, but I used it at the Intercontinental New York Barclay that charges 70,000 points per night. I pay a whopping $49 per year for that card, and I saved over $450 (plus taxes and fees) using my certificate.

For my second night, I transferred the valuable Chase Ultimate Rewards points (that I earn from Sapphire Reserve, Freedom and Freedom Unlimited cards) to World of Hyatt. I had over 4,000 Hyatt points sitting in my account, so I needed to send over another 26,000 Ultimate Rewards points to Hyatt (transferred instantaneously) to book the Park Hyatt New York City that goes for $895 per night (plus taxes and fees). Chase Ultimate Rewards points are typically valued around 2-2.1c each, but this redemption was 2.98 (call it 3) cents per point, and I got to stay in the swankiest hotel I’ve ever stepped foot into! For FREE!

To get to New York City, I looked at a few options. I could have used my Southwest Rapid Rewards points that I have sitting in my account, but I also hold the Chase Southwest Priority card that has an annual benefit of a $75 credit on flights purchased on Southwest. I had been looking for a one-way trip to buy a cash ticket on Southwest and get that automatic $75 credit, so I bought a ticket from RSW to LaGuardia for $156.80 and was only charged $81.80 for the trip. (This card comes with a $149 annual fee, so I earned back half of that fee with this flight. It also comes with 4 reimbursed upgrades to A1-A15, so I can skip the “early bird” gimmick and take my chances checking in at 24 hours ahead of the flight… if I don’t get a decent boarding position, I can buy an upgrade to the front of the boarding line, and it will be reimbursed 4x per year. Other benefits include 7,500 Rapid Reward points as a cardmember anniversary bonus, and 20% off in-flight purchases). I used UberPool to get from LaGuardia airport to the Intercontinental Barclay hotel in Manhattan for $16.99, including a $5 tip.

To get home, I am flying on JetBlue using some accumulated TrueBlue points I mostly earned from the JetBlue Plus credit card from Barclay. I got 40,000 points for only $1,000 in purchases, and I have earned smatterings of additional points from actual flights on JetBlue, filling out surveys, and doing my grocery shopping with that card. For 10,000 TrueBlue points, I flew home to Fort Myers, FL from Newark, NJ. My JetBlue credit card also gives me 50% off in-flight purchases, so I bought a Mile-High Mule and an Angry Orchard for only $3.50 each. To get to the airport, I booked a shuttle bus called the Newark Airport Express for $18 that picked me up at Bryant Park (42nd Street and 5th Avenue) and brought me to Newark in a charter bus that took about 45 minutes.

So all of the above is the “how” of travel hacking my trip, and I spent a whopping $156.79 (including $33 for parking at my home airport) for a 3-day weekend of luxury accommodations in one of the most expensive cities in the world! (I don’t count the cost of meals, since I would still be eating at home if I wasn’t traveling.) Below, I will provide a run-down of the activities I took part in, and the wonderful people I met (excluding 2 guys in Times Square that took all my remaining cash).

Saturday afternoon, upon landing at LaGuardia, I pulled out my phone to find a Twitter DM from Zero2Fire to say that she and Felicity from Fetching Financial Freedom were hanging out a café in Midtown, about ¾ mile from where my hotel was located. After checking in and dropping off my bag (traveled once again with my convertible backpack from, which I can wear like a backpack or carry like a duffel), I went to Café Zaiya and met Zero and Felicity (whom I’d met at FinCon18), where we shared an ice cream and chatted for a while, before setting out to explore the City a bit. We checked out a Japanese grocery store, where Felicity and I both bought Japanese candies), and the New York Public Library at Bryant Park, which had awesome architecture and a big gift shop.

We wandered south a little bit and saw the Flatiron Building (which was once the tallest building in the world) and we stopped at Sweaty Betty’s (women’s athleisure) and the Fujifilm store, which took our picture on their knock-off Polaroids and gave us hot chocolate and a voucher for 10 free 4×6 prints from our phones. By then, it was time to go meet The Luxe Strategist at Tacombi Flatiron, a taco joint that allowed us to sit and visit for 2 hours (it started to get crowded towards the end), before we settled up the bill, each with our own Chase Sapphire Reserve cards (I had never seen another one of these out “in the wild” until FinCon, and now it’s a regular occurrence 😉).


We walked a few blocks south to get some dessert, aka doughnuts, at a place called Dough. We stayed there until the place closed at 9, and the workers were literally taking away the chairs all around us… Haha! After walking and talking a little while longer, we said our goodbyes to Luxe, and turned to walk north towards a subway station that would take Zero and Felicity back to Zero’s apartment. By the time we split up, I only had about 10 more blocks to walk, but I ended up walking about 15 more because I got a little confused about where I was headed, but I didn’t want to make an about-face in the middle of the sidewalk, so I just continued to the next corner and turned North and walked back on the next block 😉

Saturday, I checked out of my hotel early and left my bag with the Bell Stand, then grabbed some Starbucks on my way South along Madison Avenue. I reached Madison Square Park, then walked down 5th Avenue in the direction of Washington Park.

After crossing through Washington Park,  I kept going south until I found myself surprised by the World Trade Center Memorial pools. It might sound strange to be “surprised” to be at the foot of the tallest building in North America, but I was walking through cute neighborhoods filled with a tree canopy and then all of the sudden: bam! I hit 10k steps as I was walking to the 2nd memorial pool, and then I went inside to take a little break while checking out the One World Observatory and the See Forever Theater.


After spending about an hour at the One World Observatory taking in all of the sights from 102 stories in the sky, I headed south to Battery Park to get a glimpse of the Statue of Liberty and Ellis Island. I also grabbed a $1 hotdog as I kept walking towards the Charging Bull statue. I didn’t really get close to the bull, since there was a line about 50 people deep to get your picture with the bull, unless you were a total tourist and stood at the back-end of the bull to get a picture! (Seriously, people did this!!)


Heading North on Broadway, I walked through the Wall Street area and continued north through SoHo and NoHo before reaching Union Square Park. I veered right and kept walking north on Park Avenue, ending at Grand Central Terminal. I’d been there before in 2002, but I still wanted to walk inside and marvel at the sea of humanity, all heading in different directions at different speeds, and never seeming to bump into each other. From there, I turned east and walked to the top of the Isaiah Wall in Tudor City where I took a photo of the United Nations building before heading back to the hotel to grab my bag and head towards hotel #2.

On the way to the Park Hyatt on 57th Street, I walked past Trump Tower and proceeded to extend my middle finger in protest. A few blocks later, a couple hundred steps away from my hotel, I almost bumped right into Wayne Brady, but instead of saying anything to him, I just chuckled and muttered “Wayne.”

The Park Hyatt is so fancy; you walk in and they escort you to an elevator to the lobby on the 3rd floor. I had already walked almost 29,000 steps at this point, and I was sweating from walking so much and carrying my backpack for the past 3,500 steps of that journey. I just wanted to get to my room, take a shower and rest… but I also knew I needed to take pictures to show off how fabulous these accommodations were (again, for free!). The shower was incredible, with a wand AND a rain shower in the ceiling.

I relaxed for a while in pajamas before putting on fresh clothes to go check out the Ed Sullivan Theater (Stephen Colbert), the Hello Deli (made famous by David Letterman when he was in the Ed Sullivan Theater), and I grabbed an Italian sausage sandwich from a street vendor. After finishing the sandwich, I walked south to Times Square, where I was just trying to grab a few photos before hustling out of the mob of people. I truly hate crowds, and for good reason: a street vendor/hustler came up to me, and when I said “not interested” and kept walking, he pulled the race card and said “at least shake a Black Man’s hand when you speak to him,” so I stopped and shook his hand. He was peddling crappy cd copies of his “album” and “music video” and encouraged me to follow him on YouTube. He signed the CD sleeve and so did his buddy that showed up once I stopped. I didn’t want either CD, but I didn’t want to cause a situation, either, and they both knew it… suddenly I was hit up for a “suggested donation” of $20, and I said I didn’t have any cash, so he pulled out his Square credit card reader and pointed out a police officer standing behind me saying he was legit. I didn’t want to hand over my credit card, and I didn’t want to give him anything besides his CDs back, but I took the fastest escape valve I could think of, and handed him a $20 bill and tried to walk away, but then he said “Anything for him? He’s separate” but I only had $20 left in cash and I didn’t want to give all of it away. The second guy gave me a $5 back and I scurried away, upset and nearly broke. As soon as I found a trashcan, I threw away those damn CDs and vowed that any time this happens again, I will hand back the CDs and leave, even if I must be rude about it. This situation really ruined what was otherwise a WONDERFUL day of exploring NYC.

I walked quickly back to my hotel and changed back into pajamas, content to call it a day at 5PM and just go to bed… but after a cooling off period, I decided I really wanted something to eat and to explore a tiny bit more. I saw on Google Maps that there was a Chipotle just 3 blocks away, and I had a gift card I could use to pay for it (since I no longer had enough cash). I was surprised to find that Chipotle prices in NYC aren’t that much different than Chipotle in Fort Myers, so I even had $1.18 left on the card, which I handed over to the young man in line behind me, because I’d rather give it away than try to track gift cards with $1.18 left on them. After Chipotle, I wanted a drink from Starbucks to help keep me warm on the walk back to the hotel, but after I placed my mobile order and walked next door, the lady said they were out of apple cider to make my Caramel Apple Spice. Boo! So I got a hot chocolate and went back to my room for the night.

The bed had an integrated reading light built into the headboard, which was helpful as I read a few chapters from Jen Sincero’s You Are a Badass at Making Money, before falling asleep at 9:11pm “in the City that doesn’t sleep” that the ol’ crooner Frank Sinatra used to sing about. I got over 9 hours of sleep, which wasn’t too surprising considering the 36,538 steps I walked over the course of 20.11 miles on Sunday.

Monday was a much lighter day of sight-seeing, as my legs and feet were killing me. I stayed in my room and read some more of the book before getting cleaned up and checking out of my hotel around 9:20. I left my bag with the Bell Staff again and set out for the Starbucks across the street to grab that Caramel Apple Spice that I’d wanted the night before. Starbucks in hand, I walked a couple blocks north and entered Central Park. I marveled at the City skyline from inside the park, both on the trails and atop some of the bedrock. I wandered around and saw the Wollman ice skating rink.

Then I walked along 5th Avenue on the east side of Central Park, up to 72nd Street, where I crossed through Central Park, past the Bethesda Fountain and into the Strawberry Fields (John Lennon), before escaping the park and walking south to Columbus Circle, and back to the Park Hyatt to retrieve my bag. The concierge staff seemed WAY too excited to help me with transportation, but I already had my own plans. With bag in tow, I walked 15 blocks south to Bryant Park to grab the Newark Airport Express shuttle bus, which priced out at $18 one-way, versus about $68 with Uber. To be honest, it was more comfortable on the charter bus too, so I saved $50 and had a more enjoyable trip.

Newark Airport was a breeze, getting from the curb to my gate in only 8 minutes, thanks to my TSA Pre-Check that was reimbursed by my Chase Sapphire Reserve card ($85 fee). Unfortunately my flight was delayed, so I had plenty of time to knock out this 2,700+ word blog post 😊

Highlights of the trip:

Hanging with Zero/Felicity/Luxe. No question, my FIRE friends on Twitter are my favorite people on the planet.

One World Observatory. Definitely worth the $38 bucks plus taxes/fees (41.37 in total).

Walking all over the City and never getting bored. I’m at over 65,000 steps in my ~50 hours here in the City, with over 17,000 on Saturday afternoon/evening, the aforementioned 36,500 on Sunday, and over 11,600 as I sit here writing. Most days I struggle to get to 10,000 steps, and here I am averaging over 20,000 steps per day, even with all of the time spent on planes and in airports waiting for planes.

Wayne Brady

Japanese candy

It was the best 3-day weekend I’ve ever had!

  1. So good seeing you again! 😀

    Also omg that CD scam happened to me my first time in NYC. I was able to at least say something along the lines of “you can share” when they pulled the “what about him?” line, but yeah, upsetting. 😦

    1. I should have given back the CDs and/or just dropped them on the ground and taken off! I haven’t paid $35 for two CDs in my life!! Lol, I guess now I have

    1. I’m still a little upset with myself that I didn’t start “travel hacking” years ago when I first learned about it, but I’m glad I finally did start about 2.5 years ago when I didn’t have any vacation time or paid holidays, because now I have this massive hoard of points and miles to use at my leisure! The most difficult part is I’m down here in a vacation destination, so some of my flights are more expensive than necessary because I’m competing with beach tourists for seats. Oh well, that’s the price I pay to live in Paradise 😉🌴

    1. Believe it or not, that was the standard “Long-term parking” lot at RSW. I walked from the lot to the terminal instead of taking the shuttle (and giving a nominal tip), I did the same when I landed.

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